Author's Note: For yankeedoodle74, who requested a story on how Chloe planned to pay back Oliver for the money she borrowed in Conspiracy. The suggestion for how Chloe could possibly pay back millions of dollars was to find a system at betting.

Enjoy!

BSS

Oliver folded his arms and a weary sigh left his body. He knew, after all this time, that he should never underestimate her. He knew that nothing should surprise him anymore when it came to her.

No, there really shouldn't be anything she could dole out that could shock him anymore.

And yet...

He sighed again, shaking his head. He glanced up once more, brow cinched ruefully. What was he going to do with her? Several options popped into his head, most of which involved marching straight over there and dragging her home at once, undoubtedly ignoring her kicks and screams the entire way.

He pinched the bridge of his nose. She'd never forgive him. Not in a million years.

Alternatively, he supposed, he could play along. Let her know he'd caught her without blowing her...cover, or whatever this was.

Knowing he would probably regret not going with the instincts to simply collect her and get out, Oliver swaggered over to the table, playboy facade in tact. Very slowly, hoping she didn't lose her head and throttle him across the room, he rested a hand on her shoulder.

"Hey, sweetheart."

He had to admire the fact that she didn't so much as flinch in surprise. She'd probably known he was there from the instant he walked through the doors. She spared a moment to glance up from her cards, and everyone else at the table looked over at her almost impatiently, and yet still searchingly, wanting to see if she'd give anything away. She smiled casually, not enough to make anyone think that she had an especially good hand, but then, enough to make them think things must be going relatively well for her, and stroked Oliver's hand with her own.

"Hey," she greeted back, and only Oliver saw the look in her eyes reminiscent of a child caught with her hand in the cookie jar. "What are you doing here, darling?"

"Came to get you," he said honestly, and could have kicked himself when he heard one of the players snicker. They thought he had her on a leash. "But I see you're nowhere near ready to go, yet," he added, and saw the slightly grateful look that flickered across her eyes.

"Not for a while yet, actually," she said.

"Place your bet, Green!" one of the other players grumbled irritably over at her, and Oliver hid the smirk when he realized she was masquerading as Chloe Green.

She looked at Oliver apologetically. "Meet me at the hotel room, dear?" she asked.

Oliver made a show of looking sheepish. "That was actually the real reason I cam looking for you. Locked myself out. Do you have your key?"

Chloe, who was now turned far enough in her seat that none of the other players could see her face actually grimaced. Oliver just smirked at her, holding out his hand expectantly. "Of course," she forced the words out, plucking her hotel room key from her pocket and handing it over.

Oliver's grin became still more pronounced as he pocketed the key and leaned over to plant a rather seductive kiss on her lips. Just as Chloe inhaled sharply he pulled away. "For good luck," he explained, straightening back up, eyes dancing at the slightly dazed expression on her face now.

Chloe's lips tightened and she turned back around, pushing her chips forward to place her bet.

Oliver made his exit, triumphantly patting the key in his pocket, but once he'd entered the hotel lobby elevator, he didn't head for Chloe's floor. Instead, he headed for his own room, where he donned the Green Arrow costume.

Minutes later he had infiltrated the casino's security room, where he had ample view of every angle of the casino, including Chloe's table.

Within about twenty minutes he ascertained that most of the machines were rigged, that the owner was doing some backhanded dealing under the table, and, interestingly enough, Chloe was raking in cash left and right. She wasn't cheating, though. It didn't take long to figure out she was playing it square. At one point she actually called one of the other players out on the fact that he was cheating, and moments later a pair of bouncers were escorting the extremely angry man out.

He watched her and watched her, but when it came right down to it, he really couldn't figure out what on earth she was doing there. The important thing, however, was that she was apparently holding her own just fine, and didn't seem to need him. Nothing she'd said to him earlier in person had indicated that she needed a rescue, and he knew if the Green Arrow, or even regular old Oliver Queen, came swooping in, she'd probably be not a little upset with him.

He shook his head. She was crazy. He was in love with her, but she was some kind of crazy.

He bent over and checked the pulse on the security guard he'd knocked out on his way in before taking his leave.

Even once he had returned to his street clothes, Oliver still didn't head to Chloe's hotel room. He deliberately dropped her key on the desk in the living room of his suite before heading for the shower. He knew based on what he'd seen of her game moments ago that it would be a while before she would be heading back to her room yet.

Chloe took only a grim satisfaction out of cashing in her chips. She had a cashier's check made out and folded the crisp piece of paper once before sliding it into her clutch.

Yet it was a subdued woman who headed up to her hotel room, even with the knowledge of her winnings in her purse. She wasn't exactly sure how Oliver was going to handle everything, but she doubted her gambling was going to go over well with him. She reached her door and her hand automatically went for her key.

Then she remembered she didn't have it.

Right.

She knocked on her door and waited for Oliver to open it. When she heard no movement on the other side, she began to wonder if he hadn't fallen asleep. She knocked a second time, more loudly, and called for him.

"Oliver?" she asked the door, trying not to be so loud as to disturb the people in the surrounding rooms.

She received no answer, and it finally occurred to her that Oliver must have gotten his own room and was holding her key hostage.

Typical. How am I supposed to know what room he's in? Her computer was locked in her room, so she had no convenient means of accessing the hotel database. Besides, hacking a hotel with a casino was a lot more difficult than your average Holiday Inn.

And then she remembered who she was dealing with.

With a deflated sigh, she walked back down the hall to elevator and pressed the button for the top floor. Oliver would be in the penthouse suite.

The door was even cracked open waiting for her.

Smug egotist, she thought indignantly, pushing the door open.

When she entered the room, Oliver was nowhere in sight. She spotted her key, however, lying out in the open on a desk across the room.

If she wanted to, she could be in and out of there without having to deal with Oliver.

She knew, though, that it would only delay the inevitable. She'd been caught red-handed, and Oliver was going to be demanding answers, one way or another.

Steeling herself, she closed the door.

"I think you should definitely add 'cardsharp' to your resume. That's an extremely valuable skill."

Oliver watched amusedly as he watched her unscrew herself from the ceiling. Apparently this time he had startled her. A lot.

Collecting herself, Chloe turned to face him and Oliver had his first opportunity to appreciate her choice of clothing. She certainly looked the part of the high class socialite, throwing a little money away at a poker table for fun. Silver heels and chandelier earrings accented the short, skin-tight strapless black dress she wore.

"Nice outfit," he smirked at her, eyebrow raising.

Chloe bit her lip, apparently biting back a sarcastic remark, but in the end she gave in. "Helps distract the men."

"I'll say."

"I mean at poker."

"Sure you did," Oliver grinned, enjoying being in control. Without saying anything else, Oliver turned and headed for the bedroom, knowing Chloe would follow.

Which she did, after hesitating for the briefest of moments.

Inside his room Oliver wasted no time. Within seconds he was kissing her, pulling her body against his own.

It was hardly a fair interrogation tactic, Chloe thought wryly, nearly having forgotten how good it felt to be held flush against the hard, flat planes of chest.

"I missed you," he told her, kissing her neck seductively. It was no lie, either. After a four day business trip, he had become almost desperate for her, which had increased his disappointment upon returning to Watchtower only to find she had mysteriously vanished for the weekend. Not that it had taken him too long to track her down, of course.

Chloe's guilt was preventing either of them from fully enjoying themselves however. Oliver had been about ready to forgive and forget whatever harebrained scheme this was, or at least wait until later to interrogate her. Chloe, on the other hand, had a one-track mind, and not the kind he preferred.

"The team is going to have to come bust this place up."

"Hmm," was his only response as his hands sought a hook or buttons or a zipper, anything to start getting her out of that dress.

"It's run by a mob boss."

"Mmmhmm. I knew that already." He finally found the zipper at the side of the dress and began gradually lowering it. "I learned that from about fifteen minutes," he gently nipped her neck, almost admonishingly, "of security footage."

"O-oh?" Chloe stuttered out, her head lolling back involuntarily to give him more access.

"Yeah," he said, kissing her pulse very softly, his pliant lips molding to her neck to feel her heartbeat. "Interesting thing," he added, lips still brushing against that point on her neck. "It required absolutely no poker playing to gain that information."

He actually felt her body tense in his arms.

"Right," she said uncomfortably, and Oliver felt her arms slide from his back as she awkwardly pulled herself out of his hold. She was still gripping a small silver clutch in her hand, and she snapped it open, pulling out a check and handing it to him.

Oliver stared at it blankly. "Umm..."

She waited for it to sink in, and finally, after what felt to Chloe like a very long time, it did.

"This is the exact dollar amount -"

"- that I borrowed from Queen Industries for my Kryptonite Armory," Chloe finished for him, her eyes fixing on just about anything in the room except his own.

Oliver looked from the check to Chloe and then back again. Finally he rolled his eyes. "Oh for the love of - That's what this was about?" he demanded.

Chloe, who had somehow discreetly managed to redo the zipper on her dress again, nodded.

Oliver snorted and Chloe looked at him sharply.

"I told you I was going to pay it back. This was the quickest way."

"Okay," Oliver said, heading over to the bed and flopping down on it. He crossed his ankles and folded his hands behind his head to look at her. "Setting aside the fact that I never cared about the actual money itself in the first place, let's focus on the part where you actually thought gambling was the most intelligent way to earn a lot of money."

Chloe shrugged.

He sighed and patted the spot on the bed next to him. "Get over here, Sidekick."

Feeling almost childish, Chloe crawled across the bed to lay beside him.

"So let's talk about how you could possibly have thought this was a good idea."

Chloe couldn't help it. The corner of her lip fought its way into a small smile. "I can't lose."

"That's what they all say. Are we going to have to go to those group meetings together now?"

"I'm serious. I literally can't lose."

He wrenched his neck around to look at her. "You were cheating? I watched you for ages and I never saw you do anything remotely suspicious."

"I wasn't cheating."

"Well unless you were cheating, then there's no way to guarantee you won't lose. That's why it's called a gamble."

"It's not cheating to be intelligent."

His eyes narrowed suspiciously. "This sounds a lot like it's going to be a very clever way to cheat."

Chloe bristled. "I was not cheating!" she insisted. "There is nothing in the rules about being really good at reading people."

He stared and Chloe sighed.

"I haven't decided if I should chalk it up to repressed reporter skills or to the fact that I am in on at least six earth shattering secrets, but I can detect a bluff a mile away. People are really bad at lying to me." There was no missing the slight hint of pride in her voice.

Oliver looked at her for the space of five seconds before he burst into laughter. "Oh dear God, that's hysterical!"

Chloe pushed him off. "Stop that!" she laughed, but he couldn't. Oliver laughed until his sides ached.

"I think I actually feel bad for those people," he choked out.

"Get off!" Chloe protested, for Oliver was now half on top of her.

"I love you," he sighed, wiping tears of mirth from his eyes. "You are completely insane, mind, but I adore you."

Chloe felt her cheeks flush hotly. "You're an idiot," she sighed, finally managing to heave him off of her.

Oliver laid on his back and allowed his laughter to slowly die off. With an amused sigh, he looked over at her again. "Tomorrow, I'm going to let you select a charity to put that money towards, in the meantime, would you like to get married?"

"What?" Chloe gasped, completely confused.

"Well, if we were married, we could get a joint account. Then I wouldn't have to worry about you stealing company money and you would quit worrying about paying me back for money I would have happily given you in the first place if you'd just asked."

Chloe's mouth opened and closed several times before she finally managed to respond. "We don't have to be married to get a joint account."

Oliver grinned slyly. "It was worth trying."

She punched him in the gut. "Cad," she accused.

"Wrong," he said, gathering her up in his arms and pinning her own to her sides as he kissed her. "A cad would leave money on the bedside table, not ask you to marry him," he pointed out.

"Fine," she admitted, her voice muffled against his shoulder. "A clever, sneaky cad, but a cad nonetheless."

Oliver heaved a melodramatic sigh. "One of these days, Sullivan, one of these days I'm going to get to you."

Chloe mocked his sigh and was glad he couldn't see her smile. "And what a sad state the world will be in when that day comes."